| Second Round | ||||
| Eastern Bracket | ||||
| 12/25/41 | Brooklyn Hispano | 2 : 2 (aet) | Norwegian American S.C. (NY) | |
| 1/18/42 | R | Brooklyn Hispano | 3 : 1 | Norwegian American S.C. |
| 1/1/42 | Brookhattan | 4 : 1 | Hatikvoh | |
| 1/11/42 | Baltimore S.C. | 3 : 2 | Baltimore Americans | |
| 1/18/42 | Philadelphia Americans | 4 : 1 | Philadelphia Nationals | |
| 1/18/42 | Kearny Scots | 2 : 0 | Kearny Irish | |
| 1/25/42 | St. Mary’s Celtic | 4 : 5 | German American S.C. (Phi.) | |
| Pawtucket Rangers | vs. | |||
| St. John’s | vs. | |||
| Western Bracket | ||||
| 1/4/42 | Morgan USCO (Pit.) | 5 : 0 | Heidelberg (Pit.) | |
| 1/18/42 | Becks German American S.C. (Buf.) | 1 : 3 | Bartunek Slavia (Cle.) | |
| 1/18/42 | Morgan Strasser (Pit.) | 1 : 2 | Gallatin Sport Club (Pit.) | |
| 1/25/42 | Falk Field Club (Mil.) | 3 : 0 | Wacker SC (Mil.) | |
| 2/15/42 | Chrysler SC (Det.) | 7 : 0 | United German AA (Det.) | |
| 1/18/42 | Sparta Ogden Dairy (Chi.) | 4 : 0 | Viking AA (Chi.) | |
| Thistles SC (Roch.) | vs. | |||
| 1/11/42 |
Natural Setups (St. L) | 2 : 1 |
Schumachers | |
| Third Round | ||||
| Eastern Bracket | ||||
| 1/25/42 | Brookhattan | 0 : 1 | Brooklyn Hispano | |
| 2/1/42 | Philadelphia Americans | 4 : 1 | German American S.C. | |
| 2/1/42 | Kearny Scots | 3 : 1 | Baltimore S.C. | |
| 1/25/42 | Pawtucket Rangers | 4 : 1 | St. John’s | |
| Western Bracket | ||||
| 3/1/42 | Sparta Ogden Dairy | 3 : 3 (aet) | Chrysler SC | |
| 3/15/42 | R | Chrysler SC | 2 : 2 (aet) | Spartya Ogden Dairy |
| Chrysler SC disqualified, please see explanation below | ||||
| 2/15/42 | Natural Setups (St. L) | 0 : 1 | Falk Field Club | |
| 3/15/42 | Bartunek Slavia (Cle.) | 3 : 1 | Thistles SC (Roch.) | |
| 2/22/42 | Morgan USCO | 1 : 2(aet) | Gallatin Sport Clun | |
| Quarterfinals | ||||
| 2/22/42 | Kearny Scots | 1 : 2* | Philadelphia Americans | |
| *Match abandoned in second half due to crowd entering the field after a disputed non-call in the penalty area | ||||
| 4/19/42 | R | Philadelphia Americans | 3 : 2 | Kearny Scots |
| 2/1/42 | Brooklyn Hispano | 2 : 2 (aet) | Pawtucket Rangers | |
| Stopped in extra time due to darkness. Hispano scored twice in extra time but were nullified due to the stoppage | ||||
| 2/15/42 | R | Pawtucket Rangers | 1 : 0 | Brooklyn Hispano |
| 3/29/42 | Gallatin Sport Club | 2 : 0 | Bartunek Slavia | |
| 4/12/42 | Sparta Ogden Dairy | 1 : 0 | Falk Field Club | |
| Semifinals | ||||
| 5/3/42 | 1L | Philadelphia Americans | 2 : 0 | Pawtucket Rangers |
| 5/10/42 | 2L | Pawtucket Rangers | 5 : 0(aet) | Philadelphia Americans |
| Aggregate drawn 2-2, Pawtucket Rangers advance on 5-2 aggregate after extra time | ||||
| 4/26/42 | 1L | Gallatin Sport Club | 2 : 0 | Sparta |
| 5/3/42 | 2L | Sparta | 3 : 2 | Gallatin Sport Club |
| Gallatin Sport Club advance on 4-3 aggregate | ||||
| Final | ||||
| First Leg – at Legion Field – Donora, Pennsylvania | ||||
| 5/17/42 | Gallatin Sport Club | 2 : 1 | Pawtucket Rangers | |
| Second Leg – Coates Field – Pawtucket, Rhode Island | ||||
| 5/31/42 | Pawtucket Rangers | 2 : 4 |
Gallatin Sport Club | |
| Gallatin Sport Club win National Challenge Cup on 6-3 aggregate |
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| KEY – w/o – Walkover, R – Replay, 1L – 1st Leg, 2L – 2nd Leg, 3L – 3rd Leg | ||||
| Chrysler SC-Sparta Western Quarterfinal Controversy
After the first thirty minutes of extra time in the replay, referee Jack Wilson ordered another thirty minutes, as he was under orders from the USFA that the match was to produce a winner. Sparta refused to continue playing, and Wilson awarded the match to Chrysler by forfeit. Chrysler and their supporters thought it was a ploy to avoid losing the match, since they figured the Sparta players were getting tired, and would concede the winning goal. Sparta filed a protest, stating that since Chrysler were not forced to play an extra thirty minutes in the first match, they had no reason to do so in the replay. The USFA sided with Sparta, and ordered a replay for March 29. Chrysler then made a request to push back the replay date, arguing that since they had learned of the date a mere four days before, they needed time to get their players off of WWII defense jobs. When the USFA secretary James Armstrong declared in a telegram that a failure to show for the match would “mean forfeiture of the game and also result in further drastic action”, Chrysler decided to disband and withdraw from all soccer competitions. Three days later the Detroit club reconsidered their stance and offered to play the match on April 5, but the USFA ruled that it was too late. |
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